The 2023 WNBA free agency period has had a circle around it since the new collective bargaining agreement, which included a controversial prioritization clause, was signed three years ago. Then Breanna Stewart, a two-time MVP in her prime, signed a shortened, one-year deal in 2022, her first free agency, to join a decorated group of free-agent superstars this offseason.

Her emoji-filled tweets were a fun free agency Pictionary leading into an actual word tweet and the reporting around it that added another dimension to a crucial moment for the WNBA — and makes Stewart’s free agency one of the most pivotal moments in WNBA history for more reasons than where she will sign.

Stewart, 28, tweeted Sunday that she would “love to be part of a deal that helps subsidize charter travel for the entire WNBA.” She said she would contribute her name, image and likeness, social media posts and production hours for charters so that the health and safety of players would be prioritized, “which ultimately results in a better product.”

Her call of “who’s with me?” was met with digital hand raises by the WNBA Players Association (WNBPA) as well as highly marketable players including (but certainly not limited to) Sue Bird, Elena Delle Donne, Chiney Ogwumike, Kahleah Copper, Nneka Ogwumike and Napheesa Collier. Current UConn star and NIL powerhouse Paige Bueckers also raised a hand, and Memphis Grizzlies point guard Ja Morant wrote “count me in.”

Stewart, a two-time champion with the Seattle Storm, has made charter air travel a key factor in her free agency, ESPN reported that night. That’s in part because of security concerns for Brittney Griner after the free-agent center, who is almost guaranteed to re-sign with the Phoenix Mercury, was released from a Russian prison in a prisoner swap. There are a few ways things might go down in the coming weeks, after players can sign with teams beginning Feb. 1.

Stewart has turned a free-agency period centered on a prioritization clause that forces players into tough decisions on where in the world to play into one prioritizing the athlete’s highest-interest issue and potentially forcing the WNBA’s hand. Charter flights have been an ongoing stressor in the W, and Stewart is one of the players with the most marketability, money opportunities and, therefore, power.

How she uses it and what comes of it will shift the trajectory of the WNBA.

Recap: Prioritization will determine who plays in the WNBA

The first domino will be if Stewart decides to play in the WNBA at all. There were significant wins for the players in the 2020 CBA, but those didn’t come without negotiation and hedging on other issues. Players received increased family planning benefits and better pay that nearly doubled that first season, but in return, team owners were able to put in a prioritization clause that requires players with three or more years of league experience to report to training camp on time or be fined. In 2024, players will be suspended for not reporting.

“The owners really stepped up on the compensation side for the players in this collective bargaining cycle, and I think the kind of quid pro quo for that was prioritization, showing up on time for our season,” commissioner Cathy Engelbert said ahead of the 2022 WNBA Finals.

That creates a conundrum because overseas postseasons are often not over by the time WNBA camp begins in late April, and players make the bulk of their money on those contracts. The clause is unpopular with players and especially difficult on the “middle class,” who are out of that rookie range but not making the money of a Stewart-caliber player in the W. Many of those players, as well as international stars, might choose not to return to the league in 2023.

WNBA leadership in return has touted league marketing deals, yet less than 10% of players are on them to offset what they might make overseas. While Engelbert has consistently pointed out that players can make “up to $700,000” a season, a host of stipulations and max bonuses from the league and team would need to happen for a player to reach that. The league will also not release detailed information about marketing deals, and that “middle-class” tier isn’t likely to land one, as they aren't among the most popular veterans or the up-and-coming rookies who can connect the league to collegiate fandom.

Two of the biggest stars in the league are likely not nearing that money. Stewart made a supermax contract of $228,294 in 2022 and added approximately $17,000 in merit bonuses as outlined in the CBA for All-WNBA, All-Star, All-WNBA defensive team and the Storm’s playoff finish. A’ja Wilson played on a slightly smaller contract and brought in approximately $76,000 because the Las Vegas Aces won the championship and Commissioner’s Cup, and she earned a list of accolades starting with MVP.

Stewart makes far more playing overseas (a reported $1.5 million with UMMC Ekaterinburg in 2021-22) where there are no salary caps and multitime Olympic winners can draw large paydays. She also has the benefit of marketing deals led by Puma, which continues to release new colorways for her signature shoe. It’s why she signed a one-year deal last year to contemplate if she'll return to the WNBA.

WNBA’s charter flight problem

Flying commercial has been a longtime problem for the WNBA. The Los Angeles Sparks were forced to sleep in an airport last season after delays, and the Aces opted not to play a game in 2018 after a full day of delay issues. Then there are the basic player concerns about health and safety that charter flights would avoid.

The CBA improved the flight situation by upgrading players to economy-plus or comfort seats for extra leg room. Charters would mean fewer delays, better travel arrangements in the case of shortened rest days (such as in the 2022 Finals, with travel from Las Vegas to Connecticut) and more player recovery time after flying. And while no one in the league has the fame of Griner right now, surely there are security issues when a player such as Wilson, whose face is now on bags of chips, goes through TSA.

Charters are not allowed in the CBA because they present a competitive advantage for teams that pay for them versus teams that do not. Team owner Joe Tsai was quietly paying for the New York Liberty to fly charter in late 2021 and was fined $500,000 by the board of governors for it. Sports Illustrated reported that Tsai made an unofficial proposal for default charter flights and found a way to have it compensated, but it did not have majority support from the board. The WNBA disputed that in a statement to SI: "At no point was there a New York Liberty proposal for the WNBA Board of Governors to consider offering three-years-worth of charter flights for WNBA teams. It was agreed that the Liberty would explore opportunities regarding charter flights and present it to the Board. To date, that has not happened.”

The league has provided charters in rare cases when needed, and the league paid for charters for the 2022 Finals. Estimates put charters for all 12 teams through an expanded 40-game season at anywhere between $20 million and $30 million.

NBA teams began chartering flights in the late 1980s ,and by 1991 — six years before the WNBA played its first game — there were three teams chartering all of their road trips and 20 of 27 chartering at least some. MLS, which played its first game a year before the WNBA and is a good comparison, agreed to new CBA in 2020 that requires charters for at least eight legs per season (a number that doubles in 2024) plus all postseason matches. Previously, teams were allowed to charter up to four legs (two round trips).

How Stewart can weaponize prioritization for charters

This is where Stewart — who is courting front-office personnel in Turkey, where she plays for powerhouse Fenerbahçe — can play her power cards. And it seems like that’s exactly what she’s doing with her tweet. Often, when powerful people go public, it’s because they can’t get the desired result behind closed doors.

Before Russia’s invasion of Ukraine and Griner’s detainment, it seemed like a foregone conclusion that the top players would choose lucrative overseas contracts and take summers off. Napheesa Collier said this on her podcast in 2019, but in December, she dubbed it “just not worth it.” Collier, who gave birth to her first child in 2022, is reportedly on a league marketing deal.

It has changed the dynamic for some but not others. Stewart, who welcomed a child in 2021, can opt to play an “if, then” game of “if you provide charters, then I’ll play in the WNBA.” She holds the benefit of having offered to contribute monetarily and received offers from fellow players to do the same. It makes them all look less greedy in the eyes of the public, which largely sides with team owners in disputes and believes the WNBA to be unprofitable. Stewart's move places power in the players’ hands.

Engelbert was asked ahead of the Finals if having players back in time is worth costing the league one of its better players. She mostly demurred on the answer.

“We understand the players are going to make the best decision for them and their families. We see that time and time again,” Engelbert said, in part. She ended, “But I understand, and we’re eyes wide open that some players may not choose to do that.”

If the league is moved by the thought that it could lose Stewart or if there is a player-led movement regarding charters before the CBA expires, it could talk to the board of governors to vote in accordance with allowing charters. The talk of charters has been a requirement for all, which is understandable, but it's clearly lofty in terms of price point. And not every trip might necessitate a charter. There must be an in-between option.

The players trading their NIL for an airplane deal would have to be large and substantial each season to make up the $30 million, or at least a fraction of it. Allowing charters but not requiring them for every road trip is an option that grinds competitive fairness to dust, altering the league for years to come. It could be worth it, or it could cause problems.

What available charters would mean long term

Stewart can then play an “if, then” game with teams if that’s the way the charter issue goes down. Tsai is clearly on the side of charters. Clara Wu Tsai, co-owner of the Liberty, is one of the personnel in Turkey as they chase Stewart in a way largely seen only in more established leagues such as the NBA.

Aces team owner Mark Davis, who previously pledged to find loopholes in the CBA to provide better accommodations and perks for his players, is also pro-charters. Aces head coach Becky Hammon, a former WNBA player and assistant in the NBA, called it a “glaring issue” that she wants to see “changed immediately.” Other less well-off team owners might not agree because it would hit their bottom lines.

In this scenario, high-caliber free agents such as Stewart would choose locations such as New York. It’s similar to how players are choosing teams for the benefits outside of the CBA, such as better arenas, practice courts, locker rooms and accommodations.

But not everyone can play in New York, and New York can’t afford to pay all of these top available players under the hard salary cap. Those non-charter teams would be at a disadvantage but would still be able to sign good players ranking maybe at the tippy top of the second tier or lower first tier. Talent is busting at the seams of available roster spots, so the drop-off isn’t as substantial as in seasons past. A good coach can put a team such as that at least in playoff contention.

Potentially, un-leveling the playing fields with charter flights might force the lower-level clubs to invest in the product through things like marketing or social media to grow into the top echelon. However, there is also the chance that those clubs fold. Engelbert has been very cautious about expansion teams and bringing them in before the league is financially viable. Any chance of making waves, which charter prices would do, could be a hard no.

Stewie could lead first super-team

There’s the obvious impact that Stewart, one of the best and most marketable players from her time at UConn to now in the prime of her pro career, could switch teams. Her staying in Seattle would maintain the status quo and likely include a short rebuild period following Bird’s retirement. The club currently has only Jewell Loyd and Mercedes Russell signed to contracts.

Stewart signing with a different team surrounded by superstars would shift power within the league. She’s reportedly meeting with the Minnesota Lynx, who feature former Rookie of the Year Collier, the Washington Mystics with 2019 MVP Delle Donne and the Liberty.

The Liberty are Stewart's speculated landing spot and would create the league’s first super-team built almost exclusively through free agency. Skylar Diggins-Smith signed with the Mercury to create the “Big 3,” but both Diana Taurasi and Griner were draft picks there, which is similar to the 2022 champion Aces, the Lynx dynasty and the Houston Comets dynasty.

It was rare for WNBA free agency to hold any spark since previous CBAs weren’t friendly to player movement. The 2020 CBA changed that, leading 2016 champion and legend Candace Parker to the Chicago Sky to win her hometown team its first title. Her former teammate, Chelsea Gray, also left in free agency and won a championship with the Aces last fall.

New York, an original franchise that has yet to win a championship, added 2021 MVP Jonquel Jones via a trade this month and has a healthy Sabrina Ionescu on the last year of her rookie contract. Ionescu was the Liberty’s No. 1 pick in 2020. The Liberty are also reportedly pursuing Sky champion Courtney Vandersloot to run the point and, therefore, could also bring on Allie Quigley, her wife who is mulling retirement, as a sharpshooter off the bench.

It would be a win-now move given that the Liberty will need to pay Ionescu a significant increase off her rookie contract. Jones might opt not to play in 2024, when arriving a day late means an automatic suspension. That’s still on the table for Stewart as well.